Found "Chuckles Lenart".

Achievement Guide for Chucklehead

Achievement won on 21 Oct 15TA Score for this game: 1,277
Posted on 21 October 15 at 15:38

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This achievement occurs during Episode 2 - Get Tannen

Once inside Tannen's speakeasy do the following:• Interact with Door• Interact with Caricatures. (The Caricatures near Zane, not the ones near Officer Parker) Repeat 2-3 more times until you see a picture of "Chuckles LeNart"